2-(4-Methyl-2-phenyl­piperazin-4-ium-1-yl)pyridine-3-carboxyl­ate dihydrate

Li, A.-J.; Zhang, X.-H.; Sun, W.-Q.; Zhou, X.-Q.; Liu, D.-Z.

doi:10.1107/S1600536808011288

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1234

doi:10.1107/S1600536808011288

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2-(4-Methyl-2-phenylpiperazin-4-ium-1-yl)pyridine-3-carboxylate dihydrate

Ai-Jun Li,^a ^* Xiao-Hua Zhang,^b Wen-Qian Sun,^c Xue-Qin Zhou ^c and Dong-Zhi Liu ^c

^aCollege of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, People's Republic of China, ^bDepartment of Chemical and Environmental Engineering, Hebei Chemical and Pharmaceutical College, Shijiazhuang 050026, People's Republic of China, and ^cSchool of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, People's Republic of China
^*Correspondence e-mail: liaj@yeah.net

(Received 11 January 2008; accepted 21 April 2008; online 7 June 2008)

The title compound, C₁₇H₁₉N₃O₂·2H₂O, is particularly useful in the preparation of mirtazapine, which is the active agent in a new class of antidepressants. It crystallized as a zwitterion with two molecules of water in the asymmetric unit. The crystal structure is dominated by a system of hydrogen bonds involving the positively charged N atom and both water molecules.

Related literature

For details of the synthesis see: Eiichi et al. (2002a ,b ); Metzger et al. (2004 ). For related literature, see: Singer et al. (2004 ).

Experimental

Crystal data

C₁₇H₁₉N₃O₂·2H₂O
M_r = 333.38
Monoclinic, P 2₁ /n
a = 12.730 (7) Å
b = 8.157 (4) Å
c = 16.814 (9) Å
β = 94.031 (10)°
V = 1741.6 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 (2) K
0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.978, T_max = 0.984
9611 measured reflections
3550 independent reflections
2039 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.117
S = 1.00
3550 reflections
218 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1ⁱ	0.91	1.77	2.681 (2)	178
O3—H3C⋯O4ⁱⁱ	0.87	1.92	2.781 (3)	179
O4—H4A⋯O2ⁱⁱⁱ	0.85	1.94	2.761 (2)	162
O3—H3B⋯O1	0.87	2.21	3.038 (3)	161
O4—H4B⋯N1	0.85	2.23	3.037 (3)	159
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x, y+1, z.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011288/fl2184sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808011288/fl2184Isup2.hkl

checkCIF report

Comment top

The title compound, C₁₇H₁₉N₃O₂.2H₂O, is particularly useful in the preparation of mirtazapine which is the active agent in a new class of antidepressants. It crystallized as a zwitterion with two molecues of water in the asymmetric unit (Fig 1). The central piperazine ring has a normal chair conformation. In the molecule, the dihedral angle is 81.20 between plane 1(C7 C8 C9 C10) and plane 2(C11 C12 C13 C14 C15 C16), the dihedral angle is 68.40 between plane 2(C11 C12 C13 C14 C15 C16) and plane 3(N1 C2 C3 C4 C5 C6)and the the dihedral angle is 36.90 between plane 1 and plane 3. Packing is dominated by a system of hydrogen bonds involving the positively charged nitrogen and both water molecules (Table 1, Fig. 2)

Related literature top

For details of the synthesis see: Eiichi et al. (2002a,b); Metzger et al. (2004). For related literature, see: Singer et al. (2004).

Experimental top

To 162 g of 1-butanol were added 2-(4-methyl-2-phenylpiperazine-1-yl)pyridine-3-carbonitrile(54 g, 0.2 mol) and 60.93 g of potassium hydroxide. The mixture was heated to 125 - 135 centigrade degree. (Eiichi, et al., 2002a; Eiichi, et al., 2002b; Metzger, et al., 2004) After 7 h, the reaction mixture was cooled and the butanol removed from the mixture by vacuum distilation after which fresh water and toluene were added and the two phases were separated. The water solution was neutralized with hydrochloric acid to pH=6.5–7. The water was evaporated and toluene was added. The inorganic salt were filtered and toluene solution was evaporated to dryness. Yield:52 g(90%). (Singer et al., 2004) Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of an methanol-toluene solution at room temperature over 30 days.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SMART (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, drawn with 30% probability ellipsoids.
	Fig. 2. The crystal structure of (I), viewed along a axis

2-(4-Methyl-2-phenylpiperazin-4-ium-1-yl)pyridine-3-carboxylate dihydrate top

Crystal data top

C₁₇H₁₉N₃O₂·2H₂O	F(000) = 712
M_r = 333.38	D_x = 1.271 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.730 (7) Å	Cell parameters from 1949 reflections
b = 8.157 (4) Å	θ = 3.0–22.9°
c = 16.814 (9) Å	µ = 0.09 mm⁻¹
β = 94.031 (10)°	T = 294 K
V = 1741.6 (16) Å³	Block, colorless
Z = 4	0.24 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3550 independent reflections
Radiation source: fine-focus sealed tube	2039 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 26.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −14→15
T_min = 0.978, T_max = 0.984	k = −10→9
9611 measured reflections	l = −21→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0459P)² + 0.2854P] where P = (F_o² + 2F_c²)/3
3550 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.18 e Å⁻³
7 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₇H₁₉N₃O₂·2H₂O	V = 1741.6 (16) Å³
M_r = 333.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.730 (7) Å	µ = 0.09 mm⁻¹
b = 8.157 (4) Å	T = 294 K
c = 16.814 (9) Å	0.24 × 0.20 × 0.18 mm
β = 94.031 (10)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3550 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2039 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.984	R_int = 0.051
9611 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	7 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.00	Δρ_max = 0.18 e Å⁻³
3550 reflections	Δρ_min = −0.20 e Å⁻³
218 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.23746 (11)	−0.07865 (17)	0.91677 (8)	0.0468 (4)
O2	0.09369 (12)	−0.19110 (17)	0.85735 (9)	0.0523 (4)
N1	0.01524 (12)	0.33067 (19)	0.81432 (9)	0.0336 (4)
N2	0.09094 (11)	0.12896 (18)	0.73567 (8)	0.0276 (4)
N3	0.18394 (12)	0.11644 (19)	0.58307 (8)	0.0317 (4)
H3A	0.2110	0.2203	0.5847	0.038*
C1	0.14487 (17)	−0.0721 (2)	0.88370 (10)	0.0326 (5)
C2	0.09270 (14)	0.0949 (2)	0.88117 (10)	0.0284 (4)
C3	0.06312 (16)	0.1573 (2)	0.95305 (11)	0.0377 (5)
H3	0.0816	0.1015	1.0002	0.045*
C4	0.00669 (17)	0.3009 (3)	0.95524 (12)	0.0433 (5)
H4	−0.0156	0.3411	1.0030	0.052*
C5	−0.01572 (17)	0.3828 (3)	0.88490 (12)	0.0412 (5)
H5	−0.0543	0.4795	0.8860	0.049*
C6	0.06542 (14)	0.1873 (2)	0.81196 (10)	0.0276 (4)
C7	0.20574 (14)	0.1119 (2)	0.72897 (10)	0.0322 (5)
H7A	0.2362	0.0515	0.7746	0.039*
H7B	0.2377	0.2198	0.7296	0.039*
C8	0.23032 (16)	0.0240 (2)	0.65354 (10)	0.0345 (5)
H8A	0.3060	0.0155	0.6509	0.041*
H8B	0.2013	−0.0860	0.6535	0.041*
C9	0.06793 (15)	0.1316 (2)	0.58939 (10)	0.0333 (5)
H9A	0.0367	0.0231	0.5880	0.040*
H9B	0.0375	0.1924	0.5439	0.040*
C10	0.04152 (14)	0.2186 (2)	0.66603 (10)	0.0278 (4)
H10	0.0702	0.3300	0.6658	0.033*
C11	−0.07784 (15)	0.2284 (2)	0.66480 (10)	0.0302 (5)
C12	−0.12829 (16)	0.3603 (3)	0.62727 (11)	0.0396 (5)
H12	−0.0887	0.4409	0.6042	0.048*
C13	−0.23716 (18)	0.3743 (3)	0.62352 (13)	0.0502 (6)
H13	−0.2699	0.4638	0.5981	0.060*
C14	−0.29645 (18)	0.2561 (3)	0.65735 (13)	0.0530 (6)
H14	−0.3693	0.2660	0.6556	0.064*
C15	−0.24739 (17)	0.1225 (3)	0.69391 (13)	0.0530 (6)
H15	−0.2875	0.0418	0.7164	0.064*
C16	−0.13856 (16)	0.1075 (3)	0.69733 (11)	0.0419 (5)
H16	−0.1062	0.0162	0.7215	0.050*
C17	0.20966 (18)	0.0401 (3)	0.50601 (11)	0.0486 (6)
H17A	0.1818	−0.0693	0.5028	0.073*
H17B	0.2847	0.0364	0.5033	0.073*
H17C	0.1790	0.1040	0.4624	0.073*
O3	0.40776 (15)	0.1829 (2)	0.92970 (9)	0.0746 (5)
H3B	0.3615	0.1080	0.9385	0.112*
H3C	0.4310	0.1736	0.8827	0.112*
O4	0.01683 (14)	0.6489 (2)	0.72071 (9)	0.0695 (5)
H4A	0.0391	0.7172	0.7563	0.104*
H4B	0.0095	0.5500	0.7353	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0447 (10)	0.0401 (9)	0.0542 (9)	0.0108 (7)	−0.0058 (7)	−0.0023 (7)
O2	0.0587 (11)	0.0337 (9)	0.0632 (10)	−0.0008 (8)	−0.0061 (8)	−0.0103 (8)
N1	0.0378 (10)	0.0320 (10)	0.0306 (9)	0.0057 (8)	0.0001 (7)	−0.0031 (7)
N2	0.0271 (9)	0.0327 (9)	0.0230 (8)	0.0018 (7)	0.0017 (6)	−0.0002 (7)
N3	0.0354 (10)	0.0322 (9)	0.0282 (8)	−0.0069 (7)	0.0073 (7)	−0.0036 (7)
C1	0.0419 (13)	0.0324 (12)	0.0242 (10)	0.0035 (10)	0.0065 (9)	0.0006 (9)
C2	0.0286 (11)	0.0301 (11)	0.0264 (10)	0.0013 (8)	0.0006 (8)	−0.0015 (8)
C3	0.0480 (13)	0.0394 (12)	0.0258 (10)	0.0048 (10)	0.0033 (9)	0.0010 (9)
C4	0.0550 (15)	0.0448 (13)	0.0307 (11)	0.0100 (11)	0.0075 (10)	−0.0093 (10)
C5	0.0489 (14)	0.0374 (12)	0.0373 (12)	0.0131 (10)	0.0026 (10)	−0.0088 (10)
C6	0.0261 (10)	0.0290 (11)	0.0275 (10)	−0.0016 (9)	0.0000 (8)	−0.0032 (8)
C7	0.0297 (11)	0.0376 (12)	0.0294 (10)	0.0010 (9)	0.0037 (8)	0.0016 (9)
C8	0.0356 (12)	0.0325 (11)	0.0359 (11)	0.0026 (9)	0.0066 (9)	0.0000 (9)
C9	0.0321 (11)	0.0389 (12)	0.0288 (10)	−0.0060 (9)	0.0027 (8)	−0.0013 (9)
C10	0.0297 (11)	0.0288 (10)	0.0248 (10)	−0.0026 (8)	0.0009 (8)	0.0010 (8)
C11	0.0313 (12)	0.0376 (12)	0.0215 (9)	−0.0016 (9)	−0.0004 (8)	−0.0035 (9)
C12	0.0370 (13)	0.0410 (12)	0.0401 (12)	−0.0013 (10)	−0.0026 (9)	−0.0009 (10)
C13	0.0420 (14)	0.0486 (14)	0.0579 (14)	0.0055 (11)	−0.0114 (11)	−0.0019 (12)
C14	0.0327 (13)	0.0750 (18)	0.0506 (14)	0.0020 (13)	−0.0014 (11)	−0.0101 (13)
C15	0.0366 (14)	0.0773 (18)	0.0455 (13)	−0.0175 (13)	0.0051 (10)	0.0070 (13)
C16	0.0383 (13)	0.0498 (14)	0.0373 (12)	−0.0060 (11)	−0.0002 (9)	0.0063 (10)
C17	0.0517 (14)	0.0610 (15)	0.0350 (12)	−0.0073 (12)	0.0166 (10)	−0.0150 (11)
O3	0.1035 (15)	0.0632 (12)	0.0586 (10)	−0.0064 (11)	0.0167 (9)	−0.0125 (9)
O4	0.0919 (14)	0.0659 (11)	0.0516 (10)	−0.0169 (10)	0.0098 (9)	−0.0118 (9)

Geometric parameters (Å, º) top

O1—C1	1.269 (2)	C9—C10	1.529 (2)
O2—C1	1.234 (2)	C9—H9A	0.9700
N1—C6	1.335 (2)	C9—H9B	0.9700
N1—C5	1.346 (2)	C10—C11	1.520 (3)
N2—C6	1.427 (2)	C10—H10	0.9800
N2—C7	1.480 (2)	C11—C12	1.382 (3)
N2—C10	1.482 (2)	C11—C16	1.389 (3)
N3—C8	1.491 (2)	C12—C13	1.388 (3)
N3—C9	1.493 (2)	C12—H12	0.9300
N3—C17	1.495 (2)	C13—C14	1.373 (3)
N3—H3A	0.9140	C13—H13	0.9300
C1—C2	1.514 (3)	C14—C15	1.379 (3)
C2—C3	1.388 (2)	C14—H14	0.9300
C2—C6	1.409 (2)	C15—C16	1.388 (3)
C3—C4	1.376 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.371 (3)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C7—C8	1.509 (2)	O3—H3B	0.8682
C7—H7A	0.9700	O3—H3C	0.8664
C7—H7B	0.9700	O4—H4A	0.8512
C8—H8A	0.9700	O4—H4B	0.8504
C8—H8B	0.9700

C6—N1—C5	118.28 (16)	H8A—C8—H8B	108.2
C6—N2—C7	112.85 (13)	N3—C9—C10	112.07 (14)
C6—N2—C10	115.78 (14)	N3—C9—H9A	109.2
C7—N2—C10	110.66 (13)	C10—C9—H9A	109.2
C8—N3—C9	108.89 (14)	N3—C9—H9B	109.2
C8—N3—C17	112.30 (16)	C10—C9—H9B	109.2
C9—N3—C17	111.98 (14)	H9A—C9—H9B	107.9
C8—N3—H3A	108.5	N2—C10—C11	113.90 (14)
C9—N3—H3A	107.1	N2—C10—C9	109.32 (15)
C17—N3—H3A	107.9	C11—C10—C9	106.98 (14)
O2—C1—O1	125.09 (19)	N2—C10—H10	108.8
O2—C1—C2	118.56 (18)	C11—C10—H10	108.8
O1—C1—C2	116.26 (18)	C9—C10—H10	108.8
C3—C2—C6	117.18 (17)	C12—C11—C16	118.62 (19)
C3—C2—C1	116.78 (16)	C12—C11—C10	118.64 (17)
C6—C2—C1	125.90 (16)	C16—C11—C10	122.70 (18)
C4—C3—C2	120.64 (18)	C11—C12—C13	121.0 (2)
C4—C3—H3	119.7	C11—C12—H12	119.5
C2—C3—H3	119.7	C13—C12—H12	119.5
C5—C4—C3	118.00 (18)	C14—C13—C12	120.0 (2)
C5—C4—H4	121.0	C14—C13—H13	120.0
C3—C4—H4	121.0	C12—C13—H13	120.0
N1—C5—C4	123.40 (19)	C13—C14—C15	119.7 (2)
N1—C5—H5	118.3	C13—C14—H14	120.2
C4—C5—H5	118.3	C15—C14—H14	120.2
N1—C6—C2	122.34 (16)	C14—C15—C16	120.5 (2)
N1—C6—N2	117.30 (15)	C14—C15—H15	119.8
C2—C6—N2	120.36 (16)	C16—C15—H15	119.8
N2—C7—C8	111.90 (14)	C15—C16—C11	120.2 (2)
N2—C7—H7A	109.2	C15—C16—H16	119.9
C8—C7—H7A	109.2	C11—C16—H16	119.9
N2—C7—H7B	109.2	N3—C17—H17A	109.5
C8—C7—H7B	109.2	N3—C17—H17B	109.5
H7A—C7—H7B	107.9	H17A—C17—H17B	109.5
N3—C8—C7	109.50 (16)	N3—C17—H17C	109.5
N3—C8—H8A	109.8	H17A—C17—H17C	109.5
C7—C8—H8A	109.8	H17B—C17—H17C	109.5
N3—C8—H8B	109.8	H3B—O3—H3C	111.9
C7—C8—H8B	109.8	H4A—O4—H4B	117.0

O2—C1—C2—C3	106.1 (2)	C17—N3—C8—C7	177.34 (15)
O1—C1—C2—C3	−70.7 (2)	N2—C7—C8—N3	59.1 (2)
O2—C1—C2—C6	−69.5 (3)	C8—N3—C9—C10	58.5 (2)
O1—C1—C2—C6	113.8 (2)	C17—N3—C9—C10	−176.74 (16)
C6—C2—C3—C4	2.0 (3)	C6—N2—C10—C11	−55.0 (2)
C1—C2—C3—C4	−174.01 (19)	C7—N2—C10—C11	175.00 (15)
C2—C3—C4—C5	−2.4 (3)	C6—N2—C10—C9	−174.59 (14)
C6—N1—C5—C4	3.7 (3)	C7—N2—C10—C9	55.40 (18)
C3—C4—C5—N1	−0.5 (3)	N3—C9—C10—N2	−57.03 (19)
C5—N1—C6—C2	−4.1 (3)	N3—C9—C10—C11	179.19 (15)
C5—N1—C6—N2	175.71 (16)	N2—C10—C11—C12	151.89 (16)
C3—C2—C6—N1	1.4 (3)	C9—C10—C11—C12	−87.2 (2)
C1—C2—C6—N1	176.95 (18)	N2—C10—C11—C16	−30.5 (2)
C3—C2—C6—N2	−178.48 (16)	C9—C10—C11—C16	90.4 (2)
C1—C2—C6—N2	−2.9 (3)	C16—C11—C12—C13	1.4 (3)
C7—N2—C6—N1	117.95 (18)	C10—C11—C12—C13	179.18 (17)
C10—N2—C6—N1	−11.0 (2)	C11—C12—C13—C14	0.0 (3)
C7—N2—C6—C2	−62.2 (2)	C12—C13—C14—C15	−1.0 (3)
C10—N2—C6—C2	168.87 (15)	C13—C14—C15—C16	0.6 (3)
C6—N2—C7—C8	170.43 (15)	C14—C15—C16—C11	0.8 (3)
C10—N2—C7—C8	−58.0 (2)	C12—C11—C16—C15	−1.8 (3)
C9—N3—C8—C7	−58.05 (19)	C10—C11—C16—C15	−179.48 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.91	1.77	2.681 (2)	178
O3—H3C···O4ⁱⁱ	0.87	1.92	2.781 (3)	179
O4—H4A···O2ⁱⁱⁱ	0.85	1.94	2.761 (2)	162
O3—H3B···O1	0.87	2.21	3.038 (3)	161
O4—H4B···N1	0.85	2.23	3.037 (3)	159

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉N₃O₂·2H₂O
M_r	333.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	12.730 (7), 8.157 (4), 16.814 (9)
β (°)	94.031 (10)
V (Å³)	1741.6 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.978, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	9611, 3550, 2039
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.117, 1.00
No. of reflections	3550
No. of parameters	218
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.91	1.77	2.681 (2)	177.5
O3—H3C···O4ⁱⁱ	0.87	1.92	2.781 (3)	178.9
O4—H4A···O2ⁱⁱⁱ	0.85	1.94	2.761 (2)	161.7
O3—H3B···O1	0.87	2.21	3.038 (3)	160.7
O4—H4B···N1	0.85	2.23	3.037 (3)	159.3

Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) −x+1/2, y−1/2, −z+3/2; (iii) x, y+1, z.

References

Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Eiichi, I. & Kanami, Y. (2002a). US patent 6 376 668. Google Scholar
Eiichi, I. & Kanami, Y. (2002b). US patent 6 437 120. Google Scholar
Metzger, L.. & Wizel, S. (2004). US patent 6 774 230. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singer, C., Liberman, A. & Finkelstein, N. (2004). US patent 20 040 176 591. Google Scholar

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Volume 64| Part 7| July 2008| Page o1234

doi:10.1107/S1600536808011288

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